Stereoselective synthesis of (E)-α-hydroxy-1,3-dienes via the reaction of 2,5-dihydrothiophene S,S-dioxides with carbonyl compounds

Abstract

A stereoselective synthesis of (E)-α-hydroxy-1,3-dienes, by thermal extrusion from adducts of 2,5-dihydrothiophene S,S-dioxide (1) with aldehydes and ketones, is presented and its extension to the synthesis of the dienone, (E)-tagetone, and of a 1,3,5-triene system, is illustrated.